Acta Cryst. (2010). E66, o2159 [ doi:10.1107/S1600536810029569 ]
In the title compound, C10H9NOS2, the toluene group and the 2-thioxo-1,3-thiazolidin-4-one unit are planar with r.m.s. deviations of 0.0082 and 0.0136 Å, respectively. The dihedral angle between them is 71.20 (9)°. In the crystal, the molecules are stabilized through intermolecular C-H
O contacts, forming polymeric sheets extending parallel to the (0
1) plane. C-H![[pi]](/logos/entities/pi_rmgif.gif)
contacts also occur.
The title compound has been prepared by the method described in (Shahwar et al., 2009a) and (Shahwar et al., 2009b).
All H-atoms were positioned geometrically (C–H = 0.93–0.97 Å) and refined as riding with Uiso(H) = xUeq(C), where x = 1.2 for aryl and x = 1.5 for methyl H-atoms.
Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).
![[Figure 1]](./si2279fig1thm.gif)
| Fig. 1. View of the title compound with the atom numbering scheme. The thermal ellipsoids are drawn at the 50% probability level. H-atoms are shown by small circles of arbitrary radii. |
![[Figure 2]](./si2279fig2thm.gif)
| Fig. 2. The partial packing (PLATON; Spek, 2009) which shows that molecules form polymeric sheets extending parallel to (0 1 1). |
| C10H9NOS2 | F(000) = 464 |
| Mr = 223.30 | Dx = 1.428 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2ybc | Cell parameters from 1371 reflections |
| a = 14.5885 (18) Å | θ = 3.3–25.2° |
| b = 5.5766 (6) Å | µ = 0.48 mm−1 |
| c = 12.9910 (15) Å | T = 296 K |
| β = 100.603 (6)° | Prism, light yellow |
| V = 1038.8 (2) Å3 | 0.30 × 0.20 × 0.20 mm |
| Z = 4 |
| Bruker Kappa APEXII CCD diffractometer | 1871 independent reflections |
| Radiation source: fine-focus sealed tube | 1371 reflections with I > 2σ(I) |
| graphite | Rint = 0.051 |
| Detector resolution: 8.10 pixels mm-1 | θmax = 25.2°, θmin = 3.2° |
| ω scans | h = −17→17 |
| Absorption correction: multi-scan (SADABS; Bruker, 2005) | k = −6→6 |
| Tmin = 0.939, Tmax = 0.950 | l = −14→15 |
| 7426 measured reflections |
| Refinement on F2 | Primary atom site location: structure-invariant direct methods |
| Least-squares matrix: full | Secondary atom site location: difference Fourier map |
| R[F2 > 2σ(F2)] = 0.059 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.191 | H-atom parameters constrained |
| S = 1.07 | w = 1/[σ2(Fo2) + (0.1099P)2 + 0.6595P] where P = (Fo2 + 2Fc2)/3 |
| 1871 reflections | (Δ/σ)max < 0.001 |
| 128 parameters | Δρmax = 0.45 e Å−3 |
| 0 restraints | Δρmin = −0.31 e Å−3 |
| C10H9NOS2 | V = 1038.8 (2) Å3 |
| Mr = 223.30 | Z = 4 |
| Monoclinic, P21/c | Mo Kα radiation |
| a = 14.5885 (18) Å | µ = 0.48 mm−1 |
| b = 5.5766 (6) Å | T = 296 K |
| c = 12.9910 (15) Å | 0.30 × 0.20 × 0.20 mm |
| β = 100.603 (6)° |
| Bruker Kappa APEXII CCD diffractometer | 1871 independent reflections |
| Absorption correction: multi-scan (SADABS; Bruker, 2005) | 1371 reflections with I > 2σ(I) |
| Tmin = 0.939, Tmax = 0.950 | Rint = 0.051 |
| 7426 measured reflections | θmax = 25.2° |
| R[F2 > 2σ(F2)] = 0.059 | H-atom parameters constrained |
| wR(F2) = 0.191 | Δρmax = 0.45 e Å−3 |
| S = 1.07 | Δρmin = −0.31 e Å−3 |
| 1871 reflections | Absolute structure: ? |
| 128 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
| x | y | z | Uiso*/Ueq | ||
| S1 | 0.07809 (7) | 0.7565 (2) | 0.48054 (8) | 0.0640 (4) | |
| S2 | 0.08797 (7) | 0.4645 (2) | 0.29429 (9) | 0.0645 (4) | |
| O1 | 0.29145 (18) | 1.1330 (5) | 0.45318 (19) | 0.0576 (9) | |
| N1 | 0.20548 (18) | 0.8215 (5) | 0.3708 (2) | 0.0419 (8) | |
| C1 | 0.2640 (2) | 0.7927 (6) | 0.2936 (2) | 0.0422 (10) | |
| C2 | 0.3229 (2) | 0.5995 (7) | 0.2997 (3) | 0.0486 (11) | |
| C3 | 0.3830 (3) | 0.5829 (7) | 0.2290 (3) | 0.0559 (12) | |
| C4 | 0.3849 (3) | 0.7554 (7) | 0.1539 (3) | 0.0522 (11) | |
| C5 | 0.3251 (3) | 0.9453 (8) | 0.1489 (3) | 0.0638 (14) | |
| C6 | 0.2640 (3) | 0.9667 (7) | 0.2192 (3) | 0.0561 (14) | |
| C7 | 0.4528 (3) | 0.7357 (9) | 0.0792 (3) | 0.0774 (18) | |
| C8 | 0.2270 (2) | 0.9984 (6) | 0.4471 (3) | 0.0455 (11) | |
| C9 | 0.1587 (3) | 0.9972 (8) | 0.5211 (3) | 0.0559 (12) | |
| C10 | 0.1289 (2) | 0.6787 (6) | 0.3748 (3) | 0.0470 (11) | |
| H2 | 0.32242 | 0.48179 | 0.35029 | 0.0584* | |
| H3 | 0.42296 | 0.45210 | 0.23248 | 0.0672* | |
| H5 | 0.32517 | 1.06212 | 0.09782 | 0.0767* | |
| H6 | 0.22378 | 1.09710 | 0.21555 | 0.0676* | |
| H7A | 0.48304 | 0.88736 | 0.07508 | 0.1162* | |
| H7B | 0.41973 | 0.69135 | 0.01101 | 0.1162* | |
| H7C | 0.49876 | 0.61574 | 0.10415 | 0.1162* | |
| H9A | 0.12591 | 1.14909 | 0.51789 | 0.0672* | |
| H9B | 0.19110 | 0.97175 | 0.59244 | 0.0672* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| S1 | 0.0506 (6) | 0.0820 (8) | 0.0656 (7) | −0.0038 (5) | 0.0268 (5) | −0.0086 (5) |
| S2 | 0.0524 (6) | 0.0690 (8) | 0.0715 (8) | −0.0092 (5) | 0.0097 (5) | −0.0155 (5) |
| O1 | 0.0639 (16) | 0.0610 (17) | 0.0485 (15) | −0.0104 (14) | 0.0122 (12) | −0.0037 (12) |
| N1 | 0.0403 (14) | 0.0497 (16) | 0.0369 (14) | 0.0036 (12) | 0.0106 (11) | −0.0002 (12) |
| C1 | 0.0431 (18) | 0.050 (2) | 0.0345 (16) | 0.0003 (14) | 0.0098 (13) | −0.0013 (14) |
| C2 | 0.051 (2) | 0.052 (2) | 0.0429 (19) | 0.0044 (16) | 0.0093 (15) | 0.0068 (16) |
| C3 | 0.051 (2) | 0.066 (2) | 0.052 (2) | 0.0110 (18) | 0.0132 (16) | −0.0024 (19) |
| C4 | 0.049 (2) | 0.070 (2) | 0.0395 (18) | −0.0142 (18) | 0.0133 (15) | −0.0076 (17) |
| C5 | 0.089 (3) | 0.063 (2) | 0.044 (2) | −0.003 (2) | 0.024 (2) | 0.0133 (18) |
| C6 | 0.075 (3) | 0.049 (2) | 0.047 (2) | 0.0102 (18) | 0.0185 (18) | 0.0057 (17) |
| C7 | 0.060 (3) | 0.123 (4) | 0.055 (2) | −0.022 (2) | 0.026 (2) | −0.019 (2) |
| C8 | 0.052 (2) | 0.0459 (19) | 0.0391 (18) | 0.0040 (16) | 0.0099 (15) | 0.0013 (14) |
| C9 | 0.056 (2) | 0.069 (2) | 0.045 (2) | 0.0045 (18) | 0.0150 (16) | −0.0037 (17) |
| C10 | 0.0400 (18) | 0.053 (2) | 0.048 (2) | 0.0015 (15) | 0.0080 (14) | 0.0010 (15) |
| S1—C9 | 1.798 (5) | C4—C7 | 1.513 (6) |
| S1—C10 | 1.732 (4) | C5—C6 | 1.394 (6) |
| S2—C10 | 1.627 (4) | C8—C9 | 1.507 (5) |
| O1—C8 | 1.194 (4) | C2—H2 | 0.9300 |
| N1—C1 | 1.441 (4) | C3—H3 | 0.9300 |
| N1—C8 | 1.393 (4) | C5—H5 | 0.9300 |
| N1—C10 | 1.381 (4) | C6—H6 | 0.9300 |
| C1—C2 | 1.371 (5) | C7—H7A | 0.9600 |
| C1—C6 | 1.370 (5) | C7—H7B | 0.9600 |
| C2—C3 | 1.385 (5) | C7—H7C | 0.9600 |
| C3—C4 | 1.374 (5) | C9—H9A | 0.9700 |
| C4—C5 | 1.366 (6) | C9—H9B | 0.9700 |
| S1···N1 | 2.568 (3) | C6···H9Bvii | 3.0300 |
| S1···S1i | 3.7490 (16) | C7···H3viii | 3.0200 |
| S1···S1ii | 3.6396 (16) | C8···H6 | 3.0500 |
| S2···C2 | 3.497 (3) | C8···H7Bv | 2.9800 |
| S2···C8iii | 3.651 (4) | C10···H2 | 3.1000 |
| S1···H9Aii | 3.0300 | H2···O1iii | 2.4500 |
| S2···H6iii | 3.1500 | H2···C10 | 3.1000 |
| O1···C2iv | 3.360 (5) | H3···H7C | 2.3500 |
| O1···C6 | 3.132 (5) | H3···C7ix | 3.0200 |
| O1···C7v | 3.321 (5) | H5···H7A | 2.5700 |
| O1···H2iv | 2.4500 | H5···O1x | 2.5100 |
| O1···H5vi | 2.5100 | H6···S2iv | 3.1500 |
| O1···H7Bv | 2.6100 | H6···C8 | 3.0500 |
| N1···S1 | 2.568 (3) | H7A···H5 | 2.5700 |
| C2···S2 | 3.497 (3) | H7A···H7Axi | 2.4500 |
| C2···O1iii | 3.360 (5) | H7B···O1vii | 2.6100 |
| C4···C8vii | 3.500 (5) | H7B···C2vii | 3.0800 |
| C6···O1 | 3.132 (5) | H7B···C8vii | 2.9800 |
| C7···O1vii | 3.321 (5) | H7C···H3 | 2.3500 |
| C8···S2iv | 3.651 (4) | H9A···S1ii | 3.0300 |
| C8···C4v | 3.500 (5) | H9B···C1v | 3.0200 |
| C1···H9Bvii | 3.0200 | H9B···C2v | 3.0300 |
| C2···H9Bvii | 3.0300 | H9B···C3v | 3.0400 |
| C2···H7Bv | 3.0800 | H9B···C4v | 3.0700 |
| C3···H9Bvii | 3.0400 | H9B···C5v | 3.0400 |
| C4···H9Bvii | 3.0700 | H9B···C6v | 3.0300 |
| C5···H9Bvii | 3.0400 | ||
| C9—S1—C10 | 93.85 (18) | S2—C10—N1 | 127.1 (3) |
| C1—N1—C8 | 119.3 (3) | C1—C2—H2 | 121.00 |
| C1—N1—C10 | 123.3 (3) | C3—C2—H2 | 121.00 |
| C8—N1—C10 | 117.4 (3) | C2—C3—H3 | 119.00 |
| N1—C1—C2 | 119.5 (3) | C4—C3—H3 | 119.00 |
| N1—C1—C6 | 119.3 (3) | C4—C5—H5 | 120.00 |
| C2—C1—C6 | 121.1 (3) | C6—C5—H5 | 119.00 |
| C1—C2—C3 | 118.7 (3) | C1—C6—H6 | 121.00 |
| C2—C3—C4 | 121.5 (4) | C5—C6—H6 | 120.00 |
| C3—C4—C5 | 118.7 (4) | C4—C7—H7A | 109.00 |
| C3—C4—C7 | 120.4 (4) | C4—C7—H7B | 109.00 |
| C5—C4—C7 | 120.9 (4) | C4—C7—H7C | 109.00 |
| C4—C5—C6 | 121.0 (4) | H7A—C7—H7B | 109.00 |
| C1—C6—C5 | 119.0 (4) | H7A—C7—H7C | 109.00 |
| O1—C8—N1 | 124.3 (3) | H7B—C7—H7C | 109.00 |
| O1—C8—C9 | 124.5 (3) | S1—C9—H9A | 110.00 |
| N1—C8—C9 | 111.2 (3) | S1—C9—H9B | 110.00 |
| S1—C9—C8 | 106.9 (3) | C8—C9—H9A | 110.00 |
| S1—C10—S2 | 122.26 (19) | C8—C9—H9B | 110.00 |
| S1—C10—N1 | 110.7 (2) | H9A—C9—H9B | 109.00 |
| C9—S1—C10—N1 | 1.8 (3) | C10—N1—C8—C9 | −0.3 (4) |
| C10—S1—C9—C8 | −1.9 (3) | N1—C1—C6—C5 | 176.0 (3) |
| C9—S1—C10—S2 | −178.1 (3) | C6—C1—C2—C3 | 0.1 (5) |
| C10—N1—C1—C2 | −72.1 (4) | N1—C1—C2—C3 | −175.8 (3) |
| C8—N1—C10—S2 | 178.7 (3) | C2—C1—C6—C5 | 0.0 (5) |
| C8—N1—C1—C6 | −69.3 (4) | C1—C2—C3—C4 | 0.3 (6) |
| C10—N1—C1—C6 | 111.9 (4) | C2—C3—C4—C7 | 178.6 (4) |
| C8—N1—C1—C2 | 106.7 (4) | C2—C3—C4—C5 | −0.7 (6) |
| C1—N1—C10—S1 | 177.6 (2) | C3—C4—C5—C6 | 0.9 (6) |
| C8—N1—C10—S1 | −1.2 (4) | C7—C4—C5—C6 | −178.5 (4) |
| C1—N1—C10—S2 | −2.5 (5) | C4—C5—C6—C1 | −0.5 (6) |
| C1—N1—C8—O1 | 0.7 (5) | O1—C8—C9—S1 | −178.3 (3) |
| C10—N1—C8—O1 | 179.5 (3) | N1—C8—C9—S1 | 1.5 (4) |
| C1—N1—C8—C9 | −179.1 (3) |
| Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x, −y+2, −z+1; (iii) x, y−1, z; (iv) x, y+1, z; (v) x, −y+3/2, z+1/2; (vi) x, −y+5/2, z+1/2; (vii) x, −y+3/2, z−1/2; (viii) −x+1, y+1/2, −z+1/2; (ix) −x+1, y−1/2, −z+1/2; (x) x, −y+5/2, z−1/2; (xi) −x+1, −y+2, −z. |
| Cg2 is the centroid of the C1–C6 benzene ring. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| C2—H2···O1iii | 0.93 | 2.45 | 3.360 (5) | 167 |
| C5—H5···O1x | 0.93 | 2.51 | 3.432 (5) | 169 |
| C9—H9B···Cg2v | 0.97 | 2.71 | 3.565 (4) | 147 |
| Symmetry codes: (iii) x, y−1, z; (x) x, −y+5/2, z−1/2; (v) x, −y+3/2, z+1/2. |
| Cg2 is the centroid of the C1–C6 benzene ring. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| C2—H2···O1i | 0.93 | 2.45 | 3.360 (5) | 167 |
| C5—H5···O1ii | 0.93 | 2.51 | 3.432 (5) | 169 |
| C9—H9B···Cg2iii | 0.97 | 2.71 | 3.565 (4) | 147 |
| Symmetry codes: (i) x, y−1, z; (ii) x, −y+5/2, z−1/2; (iii) x, −y+3/2, z+1/2. |
DS is grateful to the Higher Education Commission (Pakistan) for funding this project and Professor Dr Islam Ullah Khan for providing research facilities at Government College University, Lahore, Pakistan.
Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.
Shahwar, D., Tahir, M. N., Yasmeen, A., Ahmad, N. & Khan, M. A. (2009a). Acta Cryst. E65, o3014.
Shahwar, D., Tahir, M. N., Yasmeen, A., Ahmad, N. & Khan, M. A. (2009b). Acta Cryst. E65, o3016.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Spek, A. L. (2009). Acta Cryst. D65, 148–155.
In continuation to synthesize various derivatives of 2-thioxo-1,3-thiazolidin-4-one, the title compound (I, Fig. 1) is being reported.
The crystal structure of (II) 3-(2-methylphenyl)-2-thioxo-1,3-thiazolidin-4-one (Shahwar et al., 2009a) and (III) 3-(3-methylphenyl)-2-thioxo-1,3-thiazolidin-4-one (Shahwar et al., 2009b) have been published which differ from (I) due to the position of methyl group.
In (I), the toluene group A (C1—C7) and group B (N1/C8—C10/S1/S2/O1) of 2-thioxo-1,3-thiazolidin-4-one moiety are planar with maximum r. m. s. deviations of 0.0082 and 0.0136 Å, respectively. The dihedral angle between A/B is 71.20 (9)°. This value is different from 84.44 (9)° and 83.30 (3)° as observed in (II) and (III), respectively. The molecules are stabilized in the form polymeric sheets due to C—H···O type of intermolecular H-bondings and C—H···π contacts (Table 1). The polymeric sheets extend parallel to the (0 1 1) plane (Fig. 2).